Tag: 1679-47-6

1679-47-6, 3-Methyldihydrofuran-2(3H)-one is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1679-47-6

To a 2 L, 3-neck round bottom flask, equipped with a mechanic stirrer and an internal temperature controller, is added a solution of 2,4-dichlorobromobenzene (65.5 g, 290.7 mmol) in 1.1 L [OF THF] under nitrogen. The solution is cooled to-95 C with a [MEOH/LIQUID] nitrogen bath. To this solution is added t-BuLi (400 mL, 1.6 M in pentane, 639.5 mmol) slowly via syringe pump followed by the addition of a solution of [OC-METHYL-Y-BUTYROLACTONE] (43.5 g, 434.8 mmol) in THF (100 mL). The internal temperature is controlled <-80 [C.] After 1 h stirring [<-80 C,] the reaction mixture is quenched with saturated NH4C1 solution and warmed to room temperature. Water (2 L) and EtOAc (1 L) are added and separated. The aqueous layer is extracted with EtOAc (2 x 2 L). The combined organic solutions is dried [(MGSO4)] and filtered. The filtrate is concentrated in vacuo to dryness to give 80.9 g of [1- (2,] 4-dichlorophenyl) -4- hydroxy-2-methylbutan-1-one as light yellow oil. The residue is used for Swern oxidation. To a 2 L, 3-neck round bottom flask, equipped with a mechanic stirrer and an internal temperature controller, is added DMSO (104.1 mL, 1465.7 mmol) and [CH2C12] (1.1 L). The solution is cooled to-80 C with a [MEOH/LIQUID] nitrogen bath. To this solution is added oxalyl chloride (63.9 mL, 732.9 mmol) slowly via syringe pump. The mixture is stirred at-80 C for 15 min followed by the addition of a solution of the above obtained crude [1- (2,] 4-dichlorophenyl) -4-hydroxy-2- methylbutan-1-one in [CH2C12] (150 mL) slowly via syringe pump. After stirring <-70 [C] for 1 h, to the mixture is added [ET3N] (456 mL, 3271.7 mmol). The cooling bath is removed after 5 min and the mixture is stirred at room temperature for 1.5 h. The mixture is diluted with hexanes (6 L) and washed with water (6 L). The aqueous layer is extracted with hexanes (6 L). The combined organic solutions is concentrated in vacuo to dryness and the residue is subjected to column chromatography (silica gel, 1/6 EtOAc/heptane) to give 36 g (50% for two steps) of light yellow oil as the title compound [:'H] NMR (400 MHz, CDCl3) 8 9.86 (s, 1H), 7.61 (d, J= 8.3 Hz, 1H), 7.49 (d, J=2. 0 Hz, 1H), 7.37 (dd, J=2. 0,8. 3 Hz, 1H), 3.81-3. 76 (m, 1H), 3.18 (dd, [J =] 8.2, 18.6 Hz, 1H), 2.65 (dd, [J =] 5.0, 18.6 Hz, 1H), 1.21 (d, [J =] 7.3 Hz, 3H) ; 13C NMR (100 MHz, [CDC13)] [# 206. ] 1,202. 4,139. 5,139. 2,134. 4,132. 7,132. 4,129. 6,48. 8, 42.0, 18.6 ; IR (liq. ) 2974,2936, 1996,1910, 1708,1585, 1457,1374, 1228, [1191,] 1106,1064, 978,828, [810 CM'' ;] MS (CI) [NZLZ] 247 (M+), 245 (M+). As the paragraph descriping shows that 1679-47-6 is playing an increasingly important role. Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/35586; (2004); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1679-47-6,3-Methyldihydrofuran-2(3H)-one,as a common compound, the synthetic route is as follows.

In the same apparatus as in Example 1, The residue (Ir-Pt -Re catalyst (1)) obtained in Example 1, and 0.342 g (3.0 mmol) of epsilon-caprolactone were added, It was made up with 1,2-dimethoxyethane to make epsilon-caprolactone 5%. Pressurized to 8.0 MPa with hydrogen gas, the mixture was reacted at 80 C. for 2 hours with stirring. After completion of the reaction, the resulting reaction solution was cooled to room temperature, And then filtered through a syringe equipped with a membrane filter (0.45 mum). When the obtained filtrate was analyzed by gas chromatography, The conversion of epsilon-caprolactone is 100% The yield of 1,6-hexanediol was 92.3%. The selectivity was 92.3% The yield of 1-hexanol was 8.0% The selectivity was 8.0%. In Example 1A, The catalyst was added to the Ir-Pt-Re catalyst (2) prepared in Example 2, A 1,2-dimethoxyethane solution of 5% epsilon-caprolactone was added to 50% gamma-valerolactone 1, To a 2-dimethoxyethane solution (7.5 mmol of gamma-valerolactone) Except for changing the reaction time to 4 hours, The reaction was carried out in the same manner as in Example 1A. When the obtained filtrate was analyzed by gas chromatography, The conversion of gamma-valerolactone was 50.0% . The yield of 1,4-pentanediol was 40.0%. The selectivity was 80.0%. The yield of 2-pentanol was 10.1% . The same selectivity was 20.2%.

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Reference£º
Patent; UBE INDUSTRIES LIMITED; YOSHII, KIYOTAKA; YAMADA, ATSUSHI; (22 pag.)JP2015/86199; (2015); A;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

1679-47-6, 3-Methyldihydrofuran-2(3H)-one is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: ethyl 4-bromo-2-methylbutanoateTo a HBr saturated solution of EtOH (100 mL) at 0 C was added a-methyl~y- butyrolactone (3.0 mL, 31.7 mmol). The mixture was allowed to stir at rt for 3 days and then poured onto ice (500 g). After warming to rt, the mixture was extracted with Et20 (2×200 mL). The combined organic layer was further washed with H20 (300 mL) sat. NaHC03 (3×300 mL) and brine (300 mL), dried over MgSC>4, and concentrated to give the title compound, which was used without further purification: 1H NMR (500 MHz, CDC13) delta 4.15 (q, J= 7.1 Hz, 2H), 3.43 (dt, J= 1.1, 6.9 Hz, 2H), 2.68 (m, 1H), 2.26 (m, 2H)5 1.93 (m, 2H), 1.26 (t, J= 7.0 Hz, 3H), 1.19 (d, J= 7.1 Hz, 3H).

The synthetic route of 1679-47-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; NARGUND, Ravi; LO, Michael Man-Chu; YAN, Lin; HUO, Pei; FRANKLIN, Christopher; WO2011/53519; (2011); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem